US5315443A - Organic optical material - Google Patents
Organic optical material Download PDFInfo
- Publication number
- US5315443A US5315443A US08/076,882 US7688293A US5315443A US 5315443 A US5315443 A US 5315443A US 7688293 A US7688293 A US 7688293A US 5315443 A US5315443 A US 5315443A
- Authority
- US
- United States
- Prior art keywords
- radical
- weight
- ion
- optical material
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
Definitions
- This invention relates to an optical organic material, particularly an optical organic material having distinct absorption in Infra Red (IR) range and no absorption in visible range.
- IR Infra Red
- a compound containing at least one radical selected from the group consisting of carboxyl radical, phosphoric radical and sulfonic radical is incorporated into high molecular organic matrix resin, together with metal compounds mainly including Cu ++ ion, obtaining stable ionic dispersion in resin matrix without disturbing the ionic absorption characteristics.
- the present invention provides novel optical organic material containing both a compound for supplying at least one radical selected from the group consisting of carboxyl radical, phosphoric radical and sulfonic radical, and a metal compound for supplying metal ions containing 80% by weight or more of Cu ++ ion therein.
- the metal ions are to include 80% or more by weight of Cu ++ ion therein. Less than 80% of Cu ++ ion content (more than 20% of other metal ion) disturb to obtain the desired optical absorption characteristics.
- total metal ions including mainly Cu ++ ion are to be in an amount of 0.05-40% by weight of the optical material to be obtained. Less than 0.05% of the metal ion fail to obtain the desired optical absorption characteristics and more than 40 parts of the metal ion disturb homogeneous ion dispersion and the transmittancy of the optical product.
- Cu ++ ion to be dispersed uniformly in matrix resin may be supplied through any compound containing Cu ++ ion.
- the compound includes Cu acetate, Cu oxalate, Cu formate, Cu oleate, Cu stearate, Cu fumalate, Cu laurate, Cu benzoate, Cu acetylacetonate, Cu citrate, Cu cyclohexanic butylate, Cu ethylacetate, Cu benzoylacetate, the hydrates thereof, Cu chloride, Cu sulfate, Cu phosphate, Cu carbonate, Cu hydroxide, Cu ammonium chloride, etc.
- any other metal ions such as Fe, Co, Ni, Sb, Ti, K, Mn, Cd. Tl, Ce, etc. may be added depending on any desired optical absorption characteristics of the products to be obtained.
- Fe ++ ion can be effectively and conveniently used because of particular absorption in IR range.
- the compounds for supplying at least one radical selected from the group consisting of carboxylic radical, phosphoric radical and sulfonic radical include derivatives of orthophosphoric acid, sulfonic acid, carboxylic acid, formic acid, acetic acid, butyric acid, citric acid, benzoic acid, oleic acid, lauric acid, fumaric acid, stearic acid, phosphenic acid, metaphosphoric acid, diethylphosphate, phosphomolibdic acid, phenylphosphic acid, phenylphosphate, benzenesulfonic acid, and the like.
- the optical material according to the present invention can be obtained mainly by the two processes.
- One way is to mix both the ion supplying compound including Cu ++ ion and a compound having at least one radical selected from the group consisting of carboxylic radical, phosphoric radical and sulfonic radical, with a transparent organic matrix resin such as acrylic resin, polycarbonate resin, polyvinylchloride resin, nylon resin polyethylene telephthalate resin, polystyrene resin, polyolefinic resin and the derivatives thereof.
- Homogeneous mixing can be effected at a temperature more than the m.p. of the resin employed through any desired means like roller, extruder, press, calendar, followed by forming into any desired shape.
- the other way includes polymerization process wherein a monomer compound having both radicals for polymerization and for ionic stabilization are reacted with monomers of the organic matrix resin such as methylmethacrylate, etc., the radical for polymerization including acryl, methacryl, vinyl and allyl and the radical for ionic stabilization including carboxylic, phosphonic and sulfonic radical.
- an organic compound having both hydroxyl or isocyanate radical and having at least one radical selected from the group consisting of carboxylic radical, phosphoric radical and sulfonic radical may be reacted with a transparent matrix resin having radicals reactive with the above identified radicals. Transparent polymer thus obtained is then mixed with the metal compound containing Cu ++ ion.
- the transparent polymer can be also obtained by dissolving the metal compound in a monomer mixture containing monomer of the organic matrix resin like methylmethacrylate and an organic monomer compound including both radical for polymerization and for ionic stabilization before copolymerization. Then, the monomer mixture containing the metal ions is copolymerized into any desired shape.
- the organic matrix resin monomer for copolymerization may be any desired compound including methylmethacrylate, butyl acrylate, ethylmethacrylate, isopropylmethacrylate, styrene, ⁇ -methylstyrene, etc.
- the copolymer may be cross-linking and melt-moulding can not be effected.
- the cross-linking structure of the copolymer has an another advantage of less water absorption and can be formed by cutting or polishing.
- content of carboxyl, phospheric and/or sulfonic radical thus introduced into the copolymer may be varied based on desired optical absorption characteristics of product, 0.05-50 parts by weight of the radicals are preferable for 100 parts by weight of the optical product to be obtained, less than 0.05 part content disturbing Cu ++ ion stabilization and Cu ++ ion characteristics, more than 50 parts increasing water absorption resulting in unstable state of Cu ++ ion.
- reaction temp., and the reaction period of time were 15 hrs. at 50° C., 3 hrs. at 80° C. and 3 hrs. at 100° C. respectively.
- a blue transparent copolymer thus obtained contained 0.1% of Cu and 1.04% of -COOH based on methacrylic acid.
- the copolymer obtained was pressed to a plate of 1.2 mm thickness and polished the surface thereby obtaining a transparent filter of 1.0 mm thickness.
- methylmethacrylate 85 parts by weight of methylmethacrylate, 4.5 parts by weight of ⁇ -methylstyrene, and 10 parts by weight of methacrylic acid were mixed to obtain a homogeneous monomer solution. Then 1.0 part by weight of benzoyl peroxide was added thereto as a radical polymerization reaction initiator.
- reaction temp., and the reaction period of time were 15 hrs. at 50° C., 3 hrs. at 80° C. and 3 hrs. at 100° C. respectively.
- the plate surface was polished to obtain a transparent filter of 1.0 mm thickness.
- resin has 0.22% of Cu and 1.57% of -COOH based methacrylic acid.
- the mixture was pressed to a plate of 1.2 mm thickness and polished the surface obtaining a transparent filter of 1.0 mm thickness.
- reaction temp., and the reaction period of time were 15 hrs. at 50° C., 3 hrs. at 80° C. and 3 hrs. at 100° C. respectively.
- the copolymer obtained was pressed to a plate of 1.2 mm thickness and polished the surface thereby obtaining a transparent filter of 1.0 mm thickness.
- reaction temp., and the reaction period of time were 15 hrs. at 50° C., 3 hrs. at 80° C. and 3 hrs. at 100° C. respectively.
- the copolymer obtained was cut to a plate and polished the surface thereby obtaining a transparent filter of 1.0 mm thickness.
- reaction temp., and the reaction period of time were 15 hrs. at 50° C., 3 hrs. at 80° C. and 3 hrs. at 100° C. respectively.
- the copolymer obtained was pressed to a plate of 1.2 mm thickness and polished the surface thereby obtaining a transparent filter of 1.0 mm thickness.
Abstract
Description
Claims (4)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4202849A JPH069818A (en) | 1992-06-22 | 1992-06-22 | Organic optical material |
JP4-202849 | 1992-06-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5315443A true US5315443A (en) | 1994-05-24 |
Family
ID=16464214
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/076,882 Expired - Fee Related US5315443A (en) | 1992-06-22 | 1993-06-15 | Organic optical material |
Country Status (5)
Country | Link |
---|---|
US (1) | US5315443A (en) |
EP (1) | EP0575882B1 (en) |
JP (1) | JPH069818A (en) |
CA (1) | CA2098797C (en) |
DE (1) | DE69310028T2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6835914B2 (en) | 2002-11-05 | 2004-12-28 | Mattson Technology, Inc. | Apparatus and method for reducing stray light in substrate processing chambers |
WO2015089092A1 (en) * | 2013-12-10 | 2015-06-18 | Illumina, Inc. | Biosensors for biological or chemical analysis and methods of manufacturing the same |
CN105229497A (en) * | 2013-05-23 | 2016-01-06 | 富士胶片株式会社 | Near infrared ray absorbing composition, the near infrared ray cut-off filter using it and manufacture method thereof and camera module |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08271703A (en) * | 1995-03-29 | 1996-10-18 | Konica Corp | Resin lens |
JPH09208863A (en) * | 1996-01-30 | 1997-08-12 | Kureha Chem Ind Co Ltd | Heat-absorbing coating composition and method for imparting heat-absorbing property |
WO1997046897A1 (en) * | 1996-06-03 | 1997-12-11 | Kureha Kagaku Kogyo Kabushiki Kaisha | Pdp filter and pdp device |
TW445380B (en) * | 1996-10-23 | 2001-07-11 | Sumitomo Chemical Co | Plasma display front panel |
WO1998055885A1 (en) * | 1997-06-03 | 1998-12-10 | Kureha Kagaku Kogyo Kabushiki Kaisha | Optical material made of synthetic resin, optical filter, and device, spectacle lens, heat ray absorption filter, and optical fiber each provided with the filter |
JP3709261B2 (en) * | 1997-07-31 | 2005-10-26 | 呉羽化学工業株式会社 | Optical material and manufacturing method thereof |
JPH11160529A (en) * | 1997-11-21 | 1999-06-18 | Kureha Chem Ind Co Ltd | Optical filter and device equipped with it, heat ray absorbing filter, optical fiber and lens for spectacles |
JP2001253912A (en) | 2000-03-10 | 2001-09-18 | Sony Corp | Antimicrobial agent and method of producing the same |
WO2014129291A1 (en) * | 2013-02-19 | 2014-08-28 | 富士フイルム株式会社 | Near-infrared-absorbing composition, near-infrared cut-off filter using same, camera module, and manufacturing method therefor |
KR101908469B1 (en) * | 2013-02-19 | 2018-10-16 | 후지필름 가부시키가이샤 | Near-infrared absorbing composition, near-infrared blocking filter, method for producing near-infrared blocking filter, camera module and method for manufacturing camera module |
JP2014214299A (en) * | 2013-04-30 | 2014-11-17 | 旭硝子株式会社 | Near infrared light-absorbing particle, method for producing the same, fluid dispersion and article thereof |
JP6061804B2 (en) * | 2013-05-23 | 2017-01-18 | 富士フイルム株式会社 | Near-infrared absorbing composition, near-infrared cut filter using the same, and manufacturing method thereof, and camera module and manufacturing method thereof |
JP6305901B2 (en) * | 2014-01-21 | 2018-04-04 | 富士フイルム株式会社 | Near-infrared absorbing composition, near-infrared cut filter and manufacturing method thereof, and camera module and manufacturing method thereof |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3811848A (en) * | 1972-06-30 | 1974-05-21 | Du Pont | Antistatic additive compositions |
US4082710A (en) * | 1973-05-15 | 1978-04-04 | U C B, Societe Anonyme | Isocyanate-modified acrylic compositions |
US4643537A (en) * | 1984-06-05 | 1987-02-17 | Ppg Industries, Inc. | Optical filter |
US4730902A (en) * | 1985-08-13 | 1988-03-15 | Fuji Photo Film Co., Ltd. | Infrared absorbent |
US4783142A (en) * | 1985-09-13 | 1988-11-08 | Mutzhas Maximilian F | Radiation protection filter |
US4910234A (en) * | 1987-03-12 | 1990-03-20 | Nippon Paint Co., Ltd. | Disintegration type resin particles, its preparation and coating composition containing the same |
US5116113A (en) * | 1990-09-10 | 1992-05-26 | American Optical Corporation | Laser eye protective devices |
US5141915A (en) * | 1991-02-25 | 1992-08-25 | Minnesota Mining And Manufacturing Company | Dye thermal transfer sheet with anti-stick coating |
US5246782A (en) * | 1990-12-10 | 1993-09-21 | The Dow Chemical Company | Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1468953A (en) * | 1965-11-26 | 1967-02-10 | Lubrizol Corp | Metal salts of organic acids of phosphorus |
GB1268331A (en) * | 1969-01-23 | 1972-03-29 | ||
EP0131948A3 (en) * | 1983-07-15 | 1985-03-13 | Union Carbide Corporation | Sulfochlorinated olefin polymers, ionomers made therefrom and process therefor |
GB8320904D0 (en) * | 1983-08-03 | 1983-09-07 | Rubber & Plastic Res Ass | Transformations within polymers |
US4870197A (en) * | 1986-12-12 | 1989-09-26 | Exxon Chemical Patents Inc. | Method for preparing salts of polyolefinic substituted dicarboxylic acids |
JP2819767B2 (en) * | 1990-04-27 | 1998-11-05 | 住友化学工業株式会社 | Method for producing vinyl or vinylidene polymer |
-
1992
- 1992-06-22 JP JP4202849A patent/JPH069818A/en active Pending
-
1993
- 1993-06-15 US US08/076,882 patent/US5315443A/en not_active Expired - Fee Related
- 1993-06-16 EP EP93109613A patent/EP0575882B1/en not_active Expired - Lifetime
- 1993-06-16 DE DE69310028T patent/DE69310028T2/en not_active Expired - Fee Related
- 1993-06-18 CA CA002098797A patent/CA2098797C/en not_active Expired - Fee Related
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3811848A (en) * | 1972-06-30 | 1974-05-21 | Du Pont | Antistatic additive compositions |
US4082710A (en) * | 1973-05-15 | 1978-04-04 | U C B, Societe Anonyme | Isocyanate-modified acrylic compositions |
US4643537A (en) * | 1984-06-05 | 1987-02-17 | Ppg Industries, Inc. | Optical filter |
US4730902A (en) * | 1985-08-13 | 1988-03-15 | Fuji Photo Film Co., Ltd. | Infrared absorbent |
US4783142A (en) * | 1985-09-13 | 1988-11-08 | Mutzhas Maximilian F | Radiation protection filter |
US4910234A (en) * | 1987-03-12 | 1990-03-20 | Nippon Paint Co., Ltd. | Disintegration type resin particles, its preparation and coating composition containing the same |
US5116113A (en) * | 1990-09-10 | 1992-05-26 | American Optical Corporation | Laser eye protective devices |
US5246782A (en) * | 1990-12-10 | 1993-09-21 | The Dow Chemical Company | Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings |
US5141915A (en) * | 1991-02-25 | 1992-08-25 | Minnesota Mining And Manufacturing Company | Dye thermal transfer sheet with anti-stick coating |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050098552A1 (en) * | 2002-11-05 | 2005-05-12 | Timans Paul J. | Apparatus and method for reducing stray light in substrate processing chambers |
US7135656B2 (en) | 2002-11-05 | 2006-11-14 | Mattson Technology, Inc. | Apparatus and method for reducing stray light in substrate processing chambers |
US20060289434A1 (en) * | 2002-11-05 | 2006-12-28 | Timans Paul J | Apparatus and method for reducing stray light in substrate processing chambers |
US7358462B2 (en) | 2002-11-05 | 2008-04-15 | Mattson Technology, Inc. | Apparatus and method for reducing stray light in substrate processing chambers |
US6835914B2 (en) | 2002-11-05 | 2004-12-28 | Mattson Technology, Inc. | Apparatus and method for reducing stray light in substrate processing chambers |
CN105229497A (en) * | 2013-05-23 | 2016-01-06 | 富士胶片株式会社 | Near infrared ray absorbing composition, the near infrared ray cut-off filter using it and manufacture method thereof and camera module |
CN105980832A (en) * | 2013-12-10 | 2016-09-28 | 伊鲁米那股份有限公司 | Biosensors for biological or chemical analysis and methods of manufacturing the same |
KR20160096644A (en) * | 2013-12-10 | 2016-08-16 | 일루미나, 인코포레이티드 | Biosensors for biological or chemical analysis and methods of manufacturing the same |
WO2015089092A1 (en) * | 2013-12-10 | 2015-06-18 | Illumina, Inc. | Biosensors for biological or chemical analysis and methods of manufacturing the same |
US10254225B2 (en) | 2013-12-10 | 2019-04-09 | Illumina, Inc. | Biosensors for biological or chemical analysis and methods of manufacturing the same |
AU2014364006B2 (en) * | 2013-12-10 | 2019-07-11 | Illumina, Inc. | Biosensors for biological or chemical analysis and methods of manufacturing the same |
CN105980832B (en) * | 2013-12-10 | 2019-08-16 | 伊鲁米那股份有限公司 | Biosensor and its manufacturing method for biological or chemical analysis |
KR102102934B1 (en) | 2013-12-10 | 2020-04-21 | 일루미나, 인코포레이티드 | Biosensors for biological or chemical analysis and methods of manufacturing the same |
KR20200042023A (en) * | 2013-12-10 | 2020-04-22 | 일루미나, 인코포레이티드 | Biosensors for biological or chemical analysis and methods of manufacturing the same |
KR102271774B1 (en) | 2013-12-10 | 2021-06-30 | 일루미나, 인코포레이티드 | Biosensors for biological or chemical analysis and methods of manufacturing the same |
US11181478B2 (en) | 2013-12-10 | 2021-11-23 | Illumina, Inc. | Biosensors for biological or chemical analysis and methods of manufacturing the same |
US11719637B2 (en) | 2013-12-10 | 2023-08-08 | Illumina, Inc. | Biosensors for biological or chemical analysis and methods of manufacturing the same |
Also Published As
Publication number | Publication date |
---|---|
JPH069818A (en) | 1994-01-18 |
EP0575882A3 (en) | 1994-02-02 |
EP0575882A2 (en) | 1993-12-29 |
CA2098797C (en) | 2003-08-19 |
DE69310028T2 (en) | 1997-10-16 |
CA2098797A1 (en) | 1993-12-23 |
EP0575882B1 (en) | 1997-04-23 |
DE69310028D1 (en) | 1997-05-28 |
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Legal Events
Date | Code | Title | Description |
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AS | Assignment |
Owner name: TOKYO SEIHINKAIHATSU KENKYUSHO Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:TAIRA, TETSUSABURO;IKARI, MAKOTO;REEL/FRAME:006627/0981 Effective date: 19930705 |
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Year of fee payment: 4 |
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Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
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AS | Assignment |
Owner name: KUREHA CHEMICAL INDUSTRY COMPANY, LIMITED, JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:TOKYO SEIHINKAIHATSU KENYUSHO;REEL/FRAME:012745/0278 Effective date: 20020320 |
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Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
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Owner name: KUREHA CORPORATION, JAPAN Free format text: CHANGE OF NAME;ASSIGNOR:KUREHA KAGAKU KOGYO KABUSHIKI KAISHA (AKA KUREHA CHEMICAL INDUSTRY, LTD.);REEL/FRAME:016976/0847 Effective date: 20051003 |